Hydrochloric Acid → HCID 178434295, compound

HRID 2375924Notes

Reaction equation

HRID 2375924 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[NH:33][C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:22][C:23]4[CH:24]=[C:25]5[C:29](=[CH:30][CH:31]=4)[NH:28][N:27]=[C:26]5[CH3:32])[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:34]>CO>[ClH:34].[ClH:34].[ClH:34].[CH3:32][C:26]1[C:25]2[C:29](=[CH:30][CH:31]=[C:23]([NH:22][C:21]3[C:16]4[CH:15]=[C:14]([C:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=5)[NH:33][C:17]=4[N:18]=[CH:19][N:20]=3)[CH:24]=2)[NH:28][N:27]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178434298HCID 178434298, compound

Product 1

HCID 178434295HCID 178434295, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-[4-(3-methyl-1H-indazol-5-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (488 mg, 1.10 mmol) in MeOH (10 mL) was added hydrogen chloride (9M in MeOH, 2.15 mL, 19.4 mmol), the mixture was stirred at rt for 3 h and concentrated in vacuo. The residue was triturated with Et2O and dried in vacuo to give the title compound. MS (ES+): m/z 347.12 (10) [MH+]. HPLC: tR(polar—5 mins)=1.52 min (ZQ2000, polar—5 min). A purified sample was made by Gilson HPLC to record the 1H NMR spectrum. 1H NMR (DMSO-d6, 400 MHz): δ=2.34 (s, 3H), 2.47 (brs, 2H), 3.12 (brs, 2H), 3.60 (brs, 2H), 6.29 (s, 1H), 6.92 (s, 1H), 7.07 (s, 1H), 7.19 (s, 1H), 7.25 (d, 1H, J=8.4 Hz), 7.40 (d, 1H, J=8.4 Hz), 7.75 (s, 1H), 8.06 (s, 1H), 9.27 (brs, 1H), 12.73 (brs 1H).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was triturated with Et2O
  3. customdried in vacuo

Sources & evidence

ORD record
ord-660a57ed46444962ba5b974b8ce2bf7c
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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